Dating Catwoman / Literature

• Played straight in the Alterien series; despite the fact Helena is a ruthless and morally ambiguous businesswoman with criminal connections, Oberon eventually falls for her charms.
• Alcatraz Series: Attica is the heir of the Smedry clan, a family of once-royalty with magical talents who lead the fight again the evil Librarians who now rule more than half of the world. Attica falls in love with and ends up marrying a Librarian named Shasta. They're a rather more deconstructed version than usual, and by the time of the books, they've been separated for almost 13 years—although they're not actually divorced. It's clear why they don't work as a couple, but it's also clear that they still have some love for each other. When they finally do share a scene together, there's the kind of banter you'd expect from this trope.
• In Everlost and its sequels, Nick and Miss Mary Hightower.
• X-Wing Series:
  • Corran Horn and Mirax Terrik in the Rogue Squadron books. He's a former space cop turned pilot. She's a smuggler. His father was the one who finally landed her father in jail. Still, she's a smuggler on the Rebellion's side, is like a sister to his commanding officer, and doesn't smuggle anything too nasty. They make it work. Even if her father objects strongly.
  • The later Wraith Squadron books have another one between Myn Donos, the Wraiths' sniper who lost his whole squadron in an Imperial ambush, and Lara Notsil, really Gara Petothel, an Imperial spy who planted the information attracting them to the ambush. After flying with the Wraiths in disguise for a while she ends up Becoming the Mask and falling in love with him. She's forced to fake her death, but Mercy Kill reveals they eventually found each other and are Happily Married with children.
• Luke and Mara in The Thrawn Trilogy and, of course, Hand of Thrawn. He's the last of the Jedi, she's the former personal assassin of the Emperor who wiped out the Jedi (whose final assignment was to assassinate Luke). Then he rebuilds the Jedi and she becomes second in command of one of the largest criminal organizations in the galaxy. Of course, despite the Jedi theoretically being keepers of law and order, said criminal organization ends up being one of their most reliable allies and gets less and less criminal as time goes on.
  • And of course, their son Ben may perhaps become involved with a Sith girl, Vestara Khai. There's certainly high amounts of UST. Bear in mind that the Jedi and Sith have existed largely for the specific purpose of opposing each other for thousands of years, and ultimately the conflict dates to before either order actually existed.
• There's the fan-favorite of the demon Crowley and the angel Aziraphale in Terry Pratchett and Neil Gaiman's Good Omens. They're Mistaken for Gay in the book, and Word of God is that they end up sharing a cottage in South Downs. Not quite a textbook example, as by the time of the book they've decided they have more in common with one another than either of them has with his respective boss, and have an Arrangement. In addition, this is more like Asexual Life Partners, due to the very nature of angels and demons. Played straight with Anathema, who's a witch, and Newt, who's a witch-hunter, albeit a not-very-enthusiastic one.
• InCryptid: Verity and Dominic; Verity's grandparents Alice and Thomas. Both males are from the Covenant, sworn enemies of the Price-Healy family, and both end up having a Heel–Face Turn.
• John Taylor, from the Nightside novels, had a brief affair with Bad Penny, an assassin-for-hire. Upon his return from London, they wind up trying to kill each other.
• There is a short sci-fi story about a female investment banker in the future, whose job is to spend the day looking for emerging niche markets to invest in. To motivate her, she’s competing with a figure called "The Antagonist", which is strongly implied to be an AI. At the end of the story, it's revealed that The Antagonist is not only a human being, but also her husband, and it’s apparently SOP at the company they work for to pit married couples against each other. They remain Happily Married throughout.
• The Scarlet Pimpernel: Sir Percy and Marguerite Blakeney lived estranged for a year (during which the latter fell in love with his alter ego) before Marguerite's Heel Realization and redemption.
• In Harry Harrison's Stainless Steel Rat series, the first novel that introduces Angelina gets like this. At first, Jim only wishes to catch her for his boss Inskipp. After all, it's not a very good idea to have a crazy murderess flying around in a giant battleship. After he foils her initial plot, she tries to kill him. He then gets a disguise and finds her again, running a con on another planet. While in this disguise, he starts to see a different side of her. He saves her from an assassin, and they end up spending the night together. She later reveals that she knew who he was but didn't care anymore. After some psychiatric help to remove her homicidal tendencies, they end up getting married (although it's literally a Shotgun Wedding), thus the following novels no longer fit this trope.
• Tawnos and Ashnod from The Brothers' War (Magic: The Gathering) are in love, despite being generals on the opposing sides in a war.
• The only woman Hercule Poirot comes close to being romantically involved with is a highly skilled jewel thief.
• In The Three Musketeers, d'Artagnan dates Milady for a while. And really, he is the one who lies to her. This is nothing to Athos, however, as he is still legally married to Milady by the time the book takes place.
• Lymond Chronicles ... Where to begin? There is the cringe-inducing tension between Lymond and ex-from-Hell Margaret. And his night with Joleta, where it is typically ambiguous who is seducing whom. ("There is such a thing as seducing in hate".) And perhaps Guzel.... And.... And....
• Inheritance Cycle: Nasuada and Murtagh. Their attraction sparks when Murtagh is a prisoner of her father, which blossoms into serious feelings when she's captured by his master Galbotorix.
• Ayn Rand:
  • In The Fountainhead the "hatred" between critic Dominique Francon and architect Howard Roark becomes proverbial, and newspaper commentators compare it to "A Medieval vendetta." She writes articles condemning his buildings and uses all her charm to dissuade people from giving him a job. Nobody knows (though they live in New York City and are both much in the public eye) that they spend their nights together. In bed, she tells him what she had done that day to destroy his career, and he laughs - knowing this is her way of showing that she really loves him. The two thoroughly enjoy acting like arch enemies in public by day and being secret lovers by night.
  • In Atlas Shrugged the protagonist Dagny Taggart spends half the book searching for a man she calls "The Destroyer" and "The Most Dangerous Man Who Ever Lived", vowing to save the world from him. When she finally finds him (the famous John Galt), she falls in love with him at first sight, but still tries all she can to thwart him for another quarter of the book. (Rand's posthumously published Journals include a planned scene where she actually hands him over to the police and then bursts out crying when he is taken away; in the actual book, she only pretends to do it in order to save his life).
• In Jack Vance's Lyonesse trilogy, the protagonist Aillas falls in love with the haughty viking-like maiden Tatzel while being a slave at her father's castle. He escapes, comes back as a warrior king, kidnaps her, and undergoes many adventures together with her, saving her life several times. Throughout he acts as the perfect gentleman, not taking advantage of his power over her. At one moment she actually offers him sexual favors in exchange for her liberty - but Aillas, wanting a love she is unwilling and unable to give him, declines the offer and sets her free anyway. Finally, when Aillas brings his army to assault the castle, Tatzel takes up a bow and arrow and dies among the last-ditch defenders. The victorious Aillas sadly refuses to look for "the body of the valiant maiden" among the scorched bodies in the ruins of the castle and goes on to find another and more rewarding love.
• Almost every Sherlock Holmes work not by Arthur Conan Doyle, from professional novels to amateur fanfics, has this crop up between Holmes and Irene Adler, to varying degrees of intensity and success.
• Occurs in the first two books of the Elemental Assassin between the protagonist Gin and Detective Donovan Caine. While he eventually loosens up on the fact that she killed his partner (Ultimately coming to the conclusion that if he'd known how dirty his partner was, he might have killed him himself), the basic fact that she's an assassin and he's a cop creates a conflict that they're never quite able to get over despite their mutual attraction, and Donovan ultimately removes himself from temptation by transferring to a different city.
• The novel Never Leave Me by Margaret Pemberton takes place in Nazi-occupied France, and its plot features a French girl who is active in the Resistance and a German Wehrmacht officer who fall deeply in love with each other. Much against both of their wills and in complete contradiction to the mutually antagonistic national causes both of them serve, they are helpless to stop their intensive attraction to each other.
• Happens in The Stone Prince in the middle of a battle, to the point where the man retires from combat to let his hormones settle before going after the woman again.
• The Committee of Public Safety of the People's Republic of Haven in the Honor Harrington series of novels assigned Political Officers to watch over its captains and admirals, as they were terrified the Navy might try a coup. While some People's Commissioners developed a wary sort of friendship with those they were theoretically supposed to ride herd on, most did their best to generally make their assigned captain/admiral's life a living hell. Unfortunately for the Committee, though, one of those commissioners and her admiral wound up falling quite desperately in love with each other. Though the two maintained a facade of icy hostility in public, as the commissioner in question was trusted implicitly by the Committee and thus could use her position to her own ends, behind closed doors was quite a different matter. In the end, with the help of a few other key Navy personnel and their collaborative commissioners, they ended up overthrowing the committee and restoring the Republic of Haven.

• C. L. Moore's Jirel of Joiry is a feudal warrior maiden. In the story "Black God's Kiss" Guillaume the Conqueror besieges and captures Jirel's castle after a prolonged fight, kills her retainers, and captures Joiry herself. He tries to force a kiss upon her whereupon she sinks her teeth into his neck, barely missing the jugular, and later she escapes from the dungeon where she was held. Determined to find at all costs a way of destroying Guillaume, Jirel enters a dark underground world, braving countless dangers, monsters, and perilous black magic. By kissing the statue of a sinister black god she gains the power of giving Guillaume a Kiss of Death, returns to the castle, kisses Guillaume, and has the satisfaction of seeing him immediately die in great agony. Only when seeing him dead does she realize that she had been passionately in love with Guillaume all along and that now he is dead "the light had gone out of her world" - and she bursts out bitterly crying for the beloved enemy she had killed.
• In Please Don't Tell My Parents I'm a Supervillain, the villain Lucyfar (who claims to be the Archangel Lucifer) insists that she is dating the hero Gabriel (who she claims is the Archangel Gabriel). It's hard to tell if that's actually true or not. Gabriel says it isn't, but he doesn't try too hard to get rid of her when she glomps him.
  Rushing over to open it, Lucyfar squealed, "No time to talk about it. My date is here!" Seriously, she squealed. Who were the thirteen-year-olds here?
  We filed out onto the rooftop after her as a mass of white wings fluttered down out of the sky. They tucked behind Gabriel's back as he landed, only slightly out of the way.
  "So, you two are dating?" Claire asked pointedly, giving them both a hopefully questioning grin.
  Her powers didn’t do her much good this time. "Yes!" Lucyfar declared immediately, throwing herself onto Gabriel and wrapping her arms around him.
  "No," he contradicted, standing stiff and disapproving.
  "Yes!" Lucyfar repeated, nodding like a bobble-head.
  "No," Gabriel insisted, just like last time.
• In Please Don't Tell My Parents I'm a Giant Monster, we learn that Entropy, supervillain, and Pretty Bubbles, superhero, are dating even while they publicly fight.
• In A Kingdom Besieged, Jim Dasher (head of the Kingdom intelligence forces) and Franciezka Sorboz (his Roldemish counterpart) have been lovers occasionally, she's tried to kill him twice (for purely professional reasons) and as he puts it, "When you're not trying to kill me, there's no one I'd rather spend my time with".
• In Widdershins Adventures, the titular thief Widdershins falls in love with the captain of the guard, Julian Bouniard.
• Parodied in The Supervillainy Saga where Gary Karkofsky is unwittingly the ex-lover of Ultragoddess (an Expy for Supergirl). His wife becoming a superhero also puts him as the Catwoman in their relationship.
• Conan the Barbarian had several such relationships in the course of his long career. Conspicuous in the original Conan stories by Robert E. Howard is the relationship with the woman pirate Balit. She and Conan first fall in love with each other during a battle in which they face each other, sword in hand. Andrew Offut added The Sword Of Skelos where Conan has a prolonged love/hate relationship with the Zamboulan thief, spy, and swordswoman Isparana. In a climactic scene, Conan and Isparana are rolling on the desert floor, locked in what seems mortal combat, and try to kill each other - when suddenly the swords and daggers are thrown aside and they engage in intense love-making.
• Bran Mak Morn, the Pict King, one of Robert E. Howard's lesser-known characters, seeks revenge on Titus Sulla, the arrogant Roman commander who wantonly crucified a Pict. To get at the closely-guarded Roman, Mak Morn needs the help of the reptile-like "Worms of the Earth" who live in deep tunnels. And in order to make contact with them, he needs the help of Atla, a witch who is half-reptilian herself. Bran is rather repelled by her reptile side, and Atla herself is in no way fond of him - and makes it very clear. Nevertheless, her price for helping him is "to have one night of love with a King". He is willing to pay that price, along with many other things he is willing to do in order to get his revenge.
• Kushiel's Legacy inverts the timeline with Phedre and Magnificent Bastard Melisande Shahrizai. They begin with a brief liaison, which causes no end of angst after Melisande betrays the nation. They never rekindle their relationship, but continue to be attracted to each other and flirt for the rest of the series. When Melisande proposes it as part of An Offer You Can't Refuse, Phedre acknowledges that she has a weakness where Melisande is concerned. For her part, Melisande rues that she's picked up a bit of Phedre's conscience.
• The Last Adventure of Constance Verity: Connie has an on-again, off-again repartee with a ninja-thief names Hiro. Even though he sells her out or leaves her to die almost every time they meet, she still falls for his charms when he acts charming. Tia calls it out for the unhealthy, co-dependent relationship that it is, Connie admitting that she does it to cope with the fear that she isn't cut out for the normal life she says she wants so badly.
  Connie: With Hiro, everything makes sense. Everything fits. I know it's self-destructive, but I know where I stand with him. He belongs in the chaos that is my life.
  Tia: You mean your old life.
• In The Perils of Enhancegirl, the titular character is drawn into a seductive game by the thief Ocelot. This trope is ultimately subverted. They briefly pursue a relationship, but Ocelot doesn't treat Sophie very well, manipulating her Aggressive Submissive tendencies, and eventually attempting to arrange the death of a romantic rival. She loses Sophie to that rival in the end.
• The main premise of The Unexplored Summon://Blood-Sign is that Kyousuke used to be in a relationship with the White Queen, and the latter wants to rekindle this relationship at any cost. Though there are hints that, even in the present, it's not entirely one-sided. For example, Kyousuke still goes by the nickname "Alice with Rabbit", which was given to him by the White Queen to represent them always being together.
• My Vampire Older Sister and Zombie Little Sister has a relationship between a member of the Bright Cross, a Creature-Hunter Organization, and Lilith, one of the monsters they aim to fight. They eventually got married, and are the father and stepmother of the main characters.
• Carpe Jugulum: The antagonistic vampire Vlad de Magpyr is attracted to the witch Agnes Nitt, one of the heroes, because he can't read her mind due to her Split Personality. She, and particularly her other personality, can't entirely deny that he's attractive, particularly in the context of men not usually being too interested in Agnes. Still, she's too sensible to forget he's definitely a villain.
• In Captain Freedom, the titular superhero dated future villainess Kaeko Katana while they were both at the Vineyard, and they've had an on-again-off-again relationship ever since. At one point, he tries to marry her, but it does not work out. At all.
• Villains Don't Date Heroes!: This is most of the point of the series, especially the first book. Night Terror is the Anti-Villain who has conquered her entire city, then in comes the absolutely invincible Fialux, who blasts through all of Night Terror's defenses while Night Terror is still gobsmacked by how beautiful she is. By the end of the first book, they are officially dating, even if Fialux still dislikes Night Terror's methods.
• Harry Potter: There are a few cases in Hogwarts of Quidditch players dating members of the rival House teams. In Harry Potter and the Prisoner of Azkaban, Harry (Gryffindor's Seeker) has a crush on Cho Chang (Ravenclaw's Seeker), and almost asks her out as his Yule Ball date in Goblet of Fire, but is beaten to it by Cedric Diggory (Hufflepuff's Seeker and Captain, and the legit Hogwarts champion for the Triwizard Tournament). Cedric and Cho keep their relationship going afterwards until Cedric's death at the hands of Voldemort. Harry does briefly date Cho in Order of the Phoenix and has his first kiss with her, but it ends after Cho's friend Marietta Edgecombe betrays the DA to Umbridge.
• Jaine Austen Mysteries:
  • Jaine's has fallen for a couple of guys, only for them to turn out to be the killer. This includes Cameron Bannick from This Pen For Hire, Peter Connor from Death of a Neighborhood Witch, and Justin from Murder Gets a Makeover.
  • Lance has also done this with Peter Connor as well, and Graham from Death of a Neighborhood Scrooge (though the former was more hanging out with him, and ends up telling Lance he's not gay.
• Dokkoida?! combines this with the Unwanted Harem; the male superhero, his (female) Rival, and all the supervillains (who are almost all female) all live in the same apartment building and hang out together when disguised as Muggles.
• The whole premise of Maoyu. The Hero and the Demon Overlord both say Screw Destiny to their respective roles, hook up and try to find a way to end the war without gutting their respective people's economies.